Portable headphone speakers for listening to sound are in common use and can have a variety of configurations. For example, larger, heavier headphones may be circumaural (“full-size” headphones that encompass the ear) or supra-aural (typically having pads that press against the ear). Smaller, lighter-weight headphones/earphones, sometimes called “ear-fitting headphones” such as earbuds or in-ear headphones may be designed to fit within a portion of the ear. Such portable headphone speakers may be used alone, in combination with a microphone for use with a mobile communication device (e.g. a cell phone) or to amplify external sounds, as with a hearing aid. Small, ear-fitting headphones that fit in the concha bowl of the ear and direct sound into the ear canal, such as earbuds and earmolds, are preferred by some users due to their smaller size and weight relative to larger, heavier headphones that encompass the ear or press against the concha and/or pinna of the ear. The smaller, in-ear headphones or earbuds may be preferred in many instances for use during exercise or other physical activity, such as running or biking However, such activities commonly include forceful movements of the head or body that can jar small-size earpiece from the user's ear. It is desirable to have an earpiece or earmold associated with the headphone that retains the headphone in the ear while moving, and is comfortable to wear.